First time with another man


Topic: The Fateful DayA Fateful Day
The encounter that I am about to tell has stuck in my mind and I have for so long tried to put it out of my thoughts, but periodically I find myself slipping back and remembering this particular time. This all happened many years ago, but when I think about this one time, it feels like it had just happened. It may be that I wish it would happen again or that I could somehow go back and relive the experience all over again. I have mixed feeling about it, but when it creeps back into my thoughts and I end up thinking about what actually took place, it seem to go back to that fateful time in my life but then I wish again to forget.

It actually began in early spring when I was a sixteen-year-old delinquent, skipping class and hanging out at the local game room by the high school. I had been hanging out at this game room for quite some time, when I started to become good friends the owner of the game room. His name was John and he had dark hair; dark skinned and, he was much older than I was.  
Many students would hang out up at the game room during the day and sometimes into the evening. This was a place to meet friends, play games, and just hang out if you did not have anything else to do. It was also a place where you could find drugs and alcohol, if you wanted it, or to hook up with someone. I did not really notice John to much at first, but I think he must have been watching me. He probably noticed the amount of time I was spending at the game room and during this time, I think John must have decided that he would see if I could be encouraged to become friends and maybe even build a relationship with one another.
Conversations with John wee innocent. I would ask for change to play the games or sometimes a casual, “Hello” when we saw each other. As time progressed, John would sometimes give me money to play on machines when I was hanging out there and our friendship eventually grow into where he would take me out for breakfast and lunch. It was definitely nice receiving this attention and I enjoyed skipping classes to hang out at the game room.

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   When we would go out for breakfast or lunch, our conversations were always very casual, but I now know he was getting a feel for the situation and as I would later find out, he was actually building this friendship in hopes of have sex with me. John must have become a little impatient and felt it was time to test our friendship. One day, when we were out for breakfast, our simple conversation turned to a conversation about sex and girls. John asked if I had ever been with a girl and at the time, I had been with several girls but I had not gone all the way with any of them, so I said, “Yes”. We talked about what I was attracted to and he did the same, but using this line of questions, John turned the conversation to one about homosexuality. He was trying to find out what I thought about homosexuals and if I ever found other men attractive. I told him that I thought it was wrong and I never looked at other men that way. John then asked, “So you have never slept in the same bed with one of your friends, not having sex, but sleeping together?” I said, “Well, yes but that is different,” and I told him that I was only interested in girls. I still felt our conversation was rather innocent, but it was about that was all about to change. John then mentioned that he was bisexual and asked if I know what that was. I had never heard that term before and he seemed to relish the opportunity to explain that he was attracted to women and that sometimes he found men to be attractive too. I was not sure where this was leading, but John explained that if he found a woman to be attractive and she found him attractive, they sometimes slept together and would have sex. He also said that sometimes when he found another man to be attractive, and that person was attracted to him, he enjoyed sleeping with that person too. I was kind of in shock and he continued the conversation by asking what I thought about that, and I told him that I was not sure how I felt. John now had the opening he was looking for and he explained that he found me to be someone he could really talk to about stuff and that I nice looking too.

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   I did not know what to say, but he proceeded to tell me he had thoughts about wanting to sleep with me, not to have sex but to get closer to each other. This was a bold move on his part but it would ultimately tell him if I was interested at all in having sex with him, and it did pay off for him in the end. I did not know what to do or what to say. I was somewhat flattered that he thought I was good looking, but to sleep with him, I quickly said, “No, I had never thought about sleep with him. ” John then said, “We wouldn’t have to do anything, we can just lie in bed together and see how it goes. ” I was silent. What was I going to do? This man is talking about wanting to sleep with me and he is my only way back to school. I was feeling very uneasy with the situation, and I
think he knew it too. To relieve some of the stress, John said, “Don’t worry; I am not going to make you do anything you don’t want to do. ” He was trying to smooth things out now, because he realized that he had pushed the conversation to fast. He now needed to make sure I was still open to spending time with him to make sure the opportunity was still there, before we left the restaurant and he wanted to make sure I was thinking about it, because if I was interested at all, the next offer he was going to make might just change my mind. I was speechless and did not know what to say and I think he knew the subject had made me nervous. He again told me not to worry about it and as we left the restaurant, he held out his hand in hopes that I would shake it. I quickly shook his hand and we headed back to the game room. As we drove, he continued to try to smooth thing out and to make sure everything was still ok between the two of us.

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   However, his real motive was to convince me to sleep with him and to change my mind about it or at least encourage me to keep thinking about it before we got out of the car. John told me that he hoped I would think about it and he then explained that he would give me anything if I would sleep with him, anything. John mentioned giving me money, having girls for me, buying me something. He even told me he would buy me a car. I was silent all the way back to the game room and when we got there, he asked me one last time to think about it and to let him know what it would take to change my mind. He was not going to let me out of the car until I had given him an answer, so I told him I would think about it but at the time, it did not sit well with me about sleeping with another man, but I did think about it.
A few days later, I ventured back to the game room to hang out with friends and he eventually cornered me and asked if I had thought about his proposition. I told him that I had thought about it but I was still unsure about it. He said, “Come on let’s go get something to eat. ” Right then, he knew the opportunity of having sex with me was still there and in the car on our way to the restaurant, he said, “I am so glad you are thinking about it, and you have been such a good friend, what can I get for you for being such a good friend?” I just wanted to keep this on a friendly basis, so I told him I was not sure, but he was hard-pressed now to get an answer and again asked, “Come on, there has to be something you would really like to have. ” At the restaurant, we did not really talk about it much, but I knew he wanted to find out what it would take to get me in bed. He again said, “You have been such a good friend, what it is I can get for you?” I knew he was going to keep pressing for a response so I told him that I would really like to have a car. John smiled with confidence and I knew I had given him the answer he was looking for.  He casually asked, “Oh yea, what kind of car would you like to have?” I told him I was not sure, but he knew that he needed to keep this conversation going now, because he was almost there. He kept probing to know what kind of car I liked and he asked if I liked Camaros, Firebirds, Mustangs, etc.

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   and I told him I was not sure what kind I wanted. He did not want to lose this chance of getting me into bed, so as we drove back to the game room, he said to be sure to let him know what kind of car I would like to have and that he would get it for me. The conversation on the surface seemed to become innocent again and he made sure that I understood to let him know what kind of car I wanted and that he would be sure to get it, no strings attached. When he told me, No strings attached, I was seriously thinking about what kind of car I would like and not thinking that if I do tell him would I want that I would be giving him the opportunity of sleep with me, and not just once but maybe a few times. When we pulled into the parking lot, he made sure to remind me to let him know what kind of car I would like and I said I would and he immediately asked if I would be able to tell him tomorrow. I told him I would try and we got out of the car and went inside the game room.

John really had me thinking about what kind of car I would like to have and as I thought about all the different kinds of cars, but one kept coming to mind. It was a 1956 Chevy. However, in the back of my mind I thought, what would happen if I actually went through with it and told him? I was not sure, but having a car would be nice and he did say there would be no strings attached. A couple days went by before I went back up to the game room, and I tried to avoid John as best as possible, but he came up to me and asked if I had made a decision. I was not sure if I should answer, s I hesitated for a second and then I said, Yes, I had made a decision. John said, “Great, let’s go for a drive and you can tell me!” He was obviously excited as we left in his car and I told him that I would really like to have a ’56 Chevy. He told me that he would start looking for one. I then told him that I wanted it to be a two door with a V8 and I would like it to be midnight blue. He knew he had me now, all he needed to do was reel me in and he said he would get right on it.

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   A few days had passed, when one day I was up at the game room he came up to me and told me he had found the car and that he wanted to tell me about it. John was very good at building up the situation and as we drove, he started to describe it to me, and it sounded exactly like what I wanted. He told me that it just needed to be painted the mid night blue I wanted and that it was going to be ready it in a week or so. I was so excited and I wanted to see it and drive it, but now he had a question for me. In the back of my mind, I knew it was coming, but what could I do now. He said, “Well, now that I have found the car, what are you going to do for me?” I did not know what to say. John then said, “I will tell you what, you come over to my place with me tomorrow afternoon and give it a try. I was not sure at first what he was suggesting, but realized he wanted me to sleep with him. He then said, “If you don’t like it, we can stop and leave, and you can still have the car. ” He also said, you think about and let me know. I was not sure, but said I would think about it and he patted me on the leg. We returned to the game room and he told me to come by tomorrow and let him know what I want to do and I agreed. I was so excited to have a car, but in the back of my mind, I was thinking about what might happen when we got to his place, but I wanted that car and I decided I would do it.
That night, I started to think about what was going to take place the next day when we went to his place and I knew I had better be ready for anything. My first thought was, “What if I end up cumming tomorrow?” I had not masturbated for a few days and I knew the next time I was to cum, it would be a lot.

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   I did not want to cum to much for him tomorrow so I decided I had better relieve myself and that by tomorrow, I would still be able to cum for him. Then I thought about my ass and if he puts his finger in me or his cock in me, I did not want him to think I was not prepared so I made sure to take a crap before I left that morning for school and clean my ass real good too.

The next day, I went up to the game room around noon and was nervous about what was going to happen, but all I could think about was that car he promised. He came up to me and casually said, “Are you ready?” I simple replied, “Yes I am ready. ” He said, “Are you sure?” I told him that I was sure. We got in his car and headed off to his place. I was not sure where we were going and I was very nervous as we drove because I knew where this was leading me. Along the way, I think to break the tension, he asked if I was hunger and if wanted to get something to eat first. I said, No, I just wanted to get over with it. We pulled into an apartment complex not far from the school and pulled in front of an apartment, and went inside. Inside, his apartment it was small, but nicely furnished and clean looking, and as I was looking around for a place to sit, he closed the blinds in the front room and then we went into the back bedroom. As we walked down the short hallway, I noticed there was a bathroom in the hallway and across from that; there was another room with the door closed. As we entered the back bedroom, he quickly closed the blinds, making it rather dark, but some light was able to slip past the closed blinds. It was a large bedroom with a bathroom toward the back and he had a king sized bed. He sat on the edge of the bed and motioned for me to sit next to him.

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   He put his hand on my thigh and rubbing it, and telling me to relax and that everything would be all right. I simply nodded and he told me to go ahead and take off my clothes as he stood up and started walking toward the bathroom. He closed the door to the bathroom and I sat there quietly for a second. I then thought that I had better get undressing before he returns. I took of my shoes, my shirt, pants, and my socks, and piled them at the end of the bed. I decided I would leave my underwear on and I sat there waiting. Hearing the door to the bathroom open, I looked over to see him come out wearing nothing more than a long sleeved button down shirt that appeared to be unbuttoned. As he walked over to the bed, I tried to see what his body looked like and especially how big his cock was, but his shirt covered everything. John then sat next to me and noticed I still had on my underwear. He asked, “What’s wrong?” referring to me still having my underwear on, and I said, “What do you mean?” He dismissed it, realizing I was nervous about being there and he tried to lean over toward me, apparently trying to kiss me but I turned my head. John then rubbed my shoulders for a second and told me to go ahead and lay down on the bed, near the edge. He had me face toward the window as he came around to that side of the bed and knelt on the floor by me. He had me lay on my side and he started by rubbing my chest, stomach and legs. He moved me closer to the edge of the bed, spread my legs apart and started rubbing my cock through my underwear. I tried to distance my thoughts from what was going on, but as he was trying to take off my underwear, he brought my thoughts back to what was happening by asking me to help take off my underwear.

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   As I lay back down on the bed, he started fondling my cock and my balls. He took my soft cock in his mouth, sucking it, but because I was trying to distance my thoughts, I was not getting hard for him.
Frustrated, he stopped sucking and asked me if it felt ok. I told him yes, and he asked me to help him get my cock hard. I agreed to try and he started to suck and stroking my cock again. I tried to concentrate on getting hard because I knew John was not going to stop until I cum for him because that would tell him I was willing to go all the way with him. After awhile, my cock started getting hard as I focused on trying to cum in his mouth, and it was actually starting to feel good too. As I got harder, he must have felt it harden because he started stroking my cock as he sucked. It really felt good and as I got close, he started to finger my ass. This really felt good with my cock in his mouth and him fingering my ass at the same time. I knew there was no turning back for me now and soon I could feel myself near to cumming. I was ready to cum but I was still not fully hard, so I tried to hold back, but then I just wanted to get it done and I decided it was time to cum in his mouth. When I came, I think it surprised him at first, as my cock started to buck and dribble cum in his mouth. He continued to suck and pull on my cock but it was all ready starting to become soft while still in his mouth. He disappointedly said,” Is that it?” I said, “What?” and he quickly said never mind and asked if it felt good.

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   I replied with a simple, “Yes. ” He told me to lay on my stomach in the middle of the bed as he got up off the floor. I moved to the middle of the bed for him and laid there on my stomach. He was now at the end of the bed and he told me to get on all fours, like a dog and move up toward the head of the bed. I could feel him climbing on the bed behind me now and he told me that I would really need to try to relax. I could feel him inch closer to me and felt him start rubbing my ass. He told
me to take a pillow out of the bed and put my head down on it. He then told me to spread my legs a little and arch my back. I could hear him stroking his cock lubricate and then told me again to relax. I felt him start to rub my butthole with lube and he slipped a finger in my ass and started fingering my ass a little. He asked if it felt ok and told me how nice and tight I was. He then asked if I was ready and I replied, “Yes. ” He also told me it might hurt a little at first but that I should try to relax. I could now feel his hard cock against my butt hole as he tried to penetrate me. It was ok at first, but then it really started to hurt and he asked me if I was doing ok.

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   I told it hurt and I tried to pull away from him, but when I rose up on all fours he took his cock out of me and as he did,
he told me, ok and he also said that I needed try to relax more and that the hurting would eventually stop, but that I needed to relax. He said to tell him when it stopped hurting, of course so he could try again. It hurt for a little while, but I tried to delay him putting his cock in me as long as possible. He asked a couple times if I was ready to try again and finally he had waited long enough. He said, “Ok. Let’s try again, but this time I really need you to try to relax this time when I am in you. ” I agreed and he put more lubricate on my ass and proceeded to push his hard cock in my as again. Again, it hurt and I tried to have him take it out, but he refused and held on to my hips, keeping his cock in me. He then asked how I was
doing and if I was doing ok. I replied that I was ok and then he started moving his hard cock in and out of my tight hole and when he did, it started to hurt again. I told him it was hurting again and he just told me to relax. I rose up and tried to wiggle free but he again held me tight and kept his cock moving slowly in and out of me. After a short time, he again asked if I was ok and he started really moving his cock in and out fast and fast, and I could hear his body slapping against my ass. My cock was getting hard as he moved in and out of me and it even started to feel good having moving in and out of me, but suddenly I could tell he was frustrated and he stopped. He quickly explained that I need to help too and that I should move back and forth with him.


   I told him ok, and we tried again. He said, “That’s it, now keep going. ” I did and it started to feel good this time and I was really trying to get into it, because I knew he was not going to stop until he had cum in me. He reached around me as he was pounding my ass and grabbed my hard cock saying, “Oh yea, that’s it. ” Then suddenly, he quit playing with my cock and took hold of my waist. His strokes were shorter and quicker as he was fucking me and it was hard to keep the same action going, but suddenly, he pulled me close and his hard cock went deep inside me. It hurt and I tried to pull away but he held
me close and out of breath he told me, “No, don’t move!” I knew he was cumming in me and I now could feel his hard cock jerking inside me. He was breathing heavy and soon hunched over me, moving his cock in and out very slowly. He softly kissed me on the back and his weight made me go flat on my stomach. He gently whispered to me that it felt very good and asked if I was ok. I said it hurt a little, but I was ok. He then gradually tried to get back on all fours again, and I could tell by the expression in his voice that he liked watching his cock slowly pull out as my hole gapped open just long enough for him to see his cum try to bubble out before my hole slowly tightened and close back up. John He rolled off the bed telling me I had better go clean myself out and that I should use the bathroom the hall. He walked toward the back bathroom and told me to hurry back, as I got off the bed and hurriedly walked into the bathroom. I was not sure what he meant by “cleaning myself out”, so I tried to pee first and as I tried, I could feel what I thought was KY starting to ooze from my ass and  run down my leg, so I quickly sat on the toilet.

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   When I wiped my butt, I saw that it white KY and it even looked it maybe some of his cum too. I now knew what he meant by clean myself out. I really tried hard now to push out whatever was still in me and as I was pushing, it almost felt like I needed to take a shit so relaxed as I pushed and that’s when a bunch of the KY he used came out and – some of his cum too. I was a little worried about having his cum in me but what else could I do to make sure it was all out. I did not know what to do, so after a few minutes, I decided I had better go back into the bedroom and John was waiting there for me on the bed. He was still wearing only the shirt and as I approached him, I tried to look and see his cock but the shirt was covering it. He asked me if everything was ok as I sat next to him and I said that I was ok. He told me that he really liked making love to me and that he wanted to do it again. He told me to go ahead and climb on the bed and to get on all fours again with my head down on the pillow. As I did this, he quickly got on the bed behind me and smeared KY on his cock and on my ass. He said to relax again, as he pressed the head of his cock against my hole. I remember thinking, how could he hard again so soon after cumming just a few minutes ago. I was not going to let him put his dick in my ass again, but even thought I tried to not let him put it in, his cock seemed to slip right in this time. I did not know what to do. I really did not want to do it again, so I tried to tell him that it hurt so he would take his cock out of me, but he held me close and told me to relax.

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   It really did not hurt quite as bad this time, however, I had decided that if he was going to try it again that this time, I would try not to as he fucked me. He started slowly moving his cock in and out of me and it actually felt good this time, but did not move. He noticed almost right away that I was not helping and he asked what was wrong. I told him that I did not want to do it anymore and that I thought we were only going to do it once. He said, “Come, I thought you liked it. ” “Let’s do it one more time and then we’ll go. ” I thought he had told me we would only do it once and that was it, but he wanted to do it again and started forcefully pumping my ass and moving me back and forth, trying to cum a second time. I could tell he was angry, as he was trying his best to get off. It really started to feel good, and my cock was soon rock hard as he pumped my ass. The rejection of me not willing to help seemed to take the passion out of the situation and because he was so frustrated, he stopped trying to get off, took his cock out of my ass, and told me I had better go clean up again. By his reactions, I do not think he ever noticed that I had a hard on and certainly never realized that I was actually enjoying it. Dejected, he got off the bed and hurried into the bathroom to what I thought was get dressed so I hurried too. When I came back into the bedroom to get dressed, he was sitting there, still not dressed, waiting for me. He had regrouped and said, “Ok, let’s get in bed so we can sleep together for a little bit and maybe we can try it again when we wake up. ” He really wanted to keep this going and when he said this, I was confused.

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   I thought that we had already done it; he sucked my dick and he had cum in my ass too. He pulled the covers back and motioned for me to get in bed. I told him that I just wanted to go back to school and I tried to get dressed. He was upset and now he did not know what to do. He disappointedly replied ok and went into the bathroom this time to get dressed. I too got dressed in a hurry and when he finally came back out, he sat by me and touched my thigh, saying that he was sorry it did not work out, but that he really liked making love with me. He knew I was powerless right now and he asked if I would like to try it again sometime. He was my ride back to the game room and I did not know what to say, so I said. “I thought we were only going to do it once and that was it. ” He was hesitant and eventually said, “Ok, well I hope you won’t tell anyone what we did. ” How could I tell anyone what happen? I allowed this man to have sex with me and not just a blowjob, but I let him cum in my ass. I agreed not to tell anyone and we walked out of the apartment and drove back to the game room. All the way back, I was quiet and I could see him look over at me periodically. All I could think about on our way back was what had just happened. It was bothering me terribly and when I finally got home, I felt KY and cum oozing out of me, and I knew there must still be more of his cum in me.

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   I sat on the toilet pushing and pushing to get it all out. I did manage to get more KY and maybe cum out, but it had now been several hours since we did it. I decided to jump in the shower and I washed myself all over, especially my ass and my cock. When I woke up the next morning, I though that maybe it was all a dream and that it never really happened, but did it really happen and how could I tell. I went into the bathroom because I felt that I need to take a shit, and when I did, I saw KY had come out too.  It really did happen and I was very confused. What should I do? I cannot tell any one what happen, but what if he gave me some sexually transmitted disease. I did not know what to do, s I waited and kept it all quiet. A few days later, I returned to the game room to ask about the car he had promised me and upon asking him about it, he said we needed to talk about it and we got in his car and drove around. He explained that the deal was that I needed to sleep with him and that I did not want to do that. I was in shock; I let him suck my cock, fuck me and cum in ass, and now he was not going to give me the car. He then said that if I was willing to do it again and actually spend the night with him this time that we could consider the deal back on, but only if we were to do it again. I did not know what to say. I wanted the car, but did not feel I had to do it with him again. I was upset and felt used as we went back to the game room and he told me that he still had the car and if you want to try it again that he would give me the car.

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  ” I walked away and ended up staying away from the game room for a long time. When I did go back, he carried himself confidently and he was still very friendly to me, because he must have thought I was now desperate and willing to do it again to get the car. His new demeanor made it hard to bring up the fact that I was willing to try it again. John obviously wanted me to be the one to initiate the need to continue the relationship, but how was I going to do it? I now felt unwanted and fell away from the thought of get the car from him, but actually, I wanted to continue our sexual relationship.
It was now getting toward the end of the school year and this one day when I happened to be up at the game room, John went out of his way to mention that he had recently moved closer to me and that I should come over some time to visit. He had moved into an apartment on the other side of the neighborhood and the complex was a very nice one. I am quite sure he did this in hopes of rekindling the situation over the summer. He was trying to make it very easy for me to slip over to his new place at anytime and I was excited that he still wanted to be friends. I decided to go over to his new apartment one day to see what it was like and when I waked inside it was very dim. It is hard to remember this apartment but I do remember that it was quite spacious, with a large sections couch in the living room He asked me to sit down in the living room as he walked ahead of me. A feeling of uneasiness came over me, or maybe it was nervousness remembering what had happened before when we were alone, but then why was I there. I must have wanted to go over to his place for a reason and I think I was a feeling that I wanted to feel it again and maybe even go further this time. I started to feel trapped again as he sat next to me, but I could leave and walk home at anytime this time. He told me how good it was to see me again as he touched my thigh. I wanted to do it with him, again, I enjoyed it, but I felt confused.

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   What should I do? He started to rub my thigh just as he did the last time. He asked if I could stay for a while and even asked if maybe I could spend the night. He wanted me to sleep with him again and inwardly I wanted to if for no other reason than to close the deal he promised. The car never materialized and I never again had sex with him. I did try to contact him much later, but never did find him. Ever since that fateful day, I have thoughts about how the blowjob he gave me felt, how his hard cock felt inside me, and the feeling of him cumming in me, and seeing his cum too. I did want to do it more with him, feel him sucking my cock, feel his hard cock in my ass again, and this time feel his cock in my mouth and taste his cum, and feel my cock cum in his ass too, but never again had the chance 

For a long time now, I have try to find someone, the right someone to share this experience of love making with and explore my true feeling, but these days, it could have deadly consequences. I have tried to meet other men and even transsexuals to hook up and possibly feel what it is like again to have someone inside me and to feel myself inside too, but when I start to consider what might happen and what could happen, I end up not follow through. I continued to fantasize about my experience with John and about being with other men too. I think about when John sucked my cock, and how it would feel to suck someone else’s cock too, and how good it felt when John’s cock was in me and how it felt when he was cumming in me too. I have continued to fantasize about being with other men and transsexuals, but the feeling of a dildo in my ass, while masturbating gets old quick and I ant to feel the real thing again. .
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